Tetrabutylammonium Fluoride → HCID 86731606, compound

HRID 1746442Notes

Reaction equation

HRID 1746442 reaction equation
[CH3:1][C:2]1[C:6]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]([CH2:44][CH:45]([CH3:47])[CH3:46])[C:19]3[CH:24]=[CH:23][C:22]([CH:25]([CH2:35][O:36][Si](C)(C)C(C)(C)C)[CH2:26][O:27][Si](C)(C)C(C)(C)C)=[CH:21][CH:20]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:48])[O:4][N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[OH:27][CH2:26][CH:25]([C:22]1[CH:21]=[CH:20][C:19]([N:18]([CH2:44][CH:45]([CH3:47])[CH3:46])[S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH2:8][O:7][C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:48])=[CH:10][CH:11]=2)(=[O:17])=[O:16])=[CH:24][CH:23]=1)[CH2:35][OH:36]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86731607HCID 86731607, compound

Product 1

HCID 86731606HCID 86731606, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(((3,5-dimethylisoxazol-4-yl)oxy)methyl)-N-isobutyl-N-(4-(2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-6-yl)phenyl)benzenesulfonamide (214.7 mg, 0.299 mmol) in tetrahydrofuran (THF) (10 mL) was added TBAF (1 M in THF, 0.748 mL, 0.748 mmol), and this was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and extracted to the organic phase of an aqueous workup between ethyl acetate and water/brine. The organic phase was separated (hydrophobic frit), then concentrated in vacuo and purified by flash silica (Si) chromatography (using a 0-100% ethyl acetate-cyclohexane gradient). The product containing fractions were combined and condensed, then freeze-dried to provide 76.4 mg of desired product. LCMS (M+1) 489, RT 1.02 mins.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted to the organic phase of an aqueous workup between ethyl acetate and water/brine
  3. customThe organic phase was separated (hydrophobic frit)
  4. concentrationconcentrated in vacuo
  5. custompurified by flash silica (Si) chromatography (
  6. additionThe product containing fractions
  7. customcondensed
  8. customfreeze-dried

Sources & evidence

ORD record
ord-b79095284fb445458e663fd2e24a971e
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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